Drotaverine

Title: Drotaverine
CAS Registry Number: 14009-24-6
CAS Name: 1-[(3,4-Diethoxyphenyl)methylene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline
Additional Names: 1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline; isodihydroperparine
Molecular Formula: C24H31NO4
Molecular Weight: 397.51
Percent Composition: C 72.52%, H 7.86%, N 3.52%, O 16.10%
Literature References: Analogue of papaverine, q.v. Prepn: BE 621917 (1962 to Chinoin), C.A. 59, 8713g (1963). Synthesis: E. Koltai et al., J. Labelled Compd. Radiopharm. 16, 351 (1979). Crystal structure: Z. Böcksei et al., Acta Crystallogr. C51, 1587 (1995). Absorption study: P. Szentmiklosi, S. Marton, Pharmazie 38, 611 (1983). Platelet aggregation and hemorrheological effects: Z. Kapui et al., Thromb. Res. 66, 693 (1992). Clinical pharmacokinetics and bioavailability: O. O. Bolaji et al., Eur. J. Drug Metab. Pharmacokinet. 21, 217 (1996). HPLC determn in biological fluids: eidem, J. Chromatogr. 622, 93 (1993). Clinical evaluation: D. Vecsey, Ther. Hung. 32, 127 (1984). Clinical effects on fetal development: A. E. Czeizel, M. Rockenbauer, Prenatal Neonat. Med. 1, 137 (1996).
Derivative Type: Acephyllinate
CAS Registry Number: 61954-97-0
Additional Names: Drotaverine theophylline-7-acetic acid; 6,7,3¢,4¢-tetraethoxy-1-benzyl-3,4-dihydroisoquinoline xanthine-7-acetate; DRA
Trademarks: Depogen (Chinoin)
Molecular Formula: C24H31NO4.C9H10N4O4
Molecular Weight: 635.71
Percent Composition: C 62.35%, H 6.50%, N 11.02%, O 20.13%
Properties: Exists as monohydrate.
Derivative Type: Hydrochloride
CAS Registry Number: 985-12-6
Trademarks: No-Spa (Chinoin)
Properties: Pale yellow crystals from ethanol, mp 197-200° (uncorr).
Melting point: mp 197-200° (uncorr)
Therap-Cat: Antispasmodic.
Keywords: Antispasmodic.
Drotebanol Droxicam Droxidopa DSPA DTAF

Drotaverine
Drotaverine.svg
Drotaverine ball-and-stick.png
Systematic (IUPAC) name
(Z)-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability Highly variable
Protein binding 80 to 95%
Metabolism Hepatic
Half-life 7 to 12 hours
Excretion Fecal and renal
Identifiers
CAS number 985-12-6 YesY
ATC code A03AD02
PubChem CID 1712095
DrugBank DB06751
ChemSpider 1361582 YesY
UNII 98QS4N58TW YesY
KEGG D07879 YesY
ChEMBL CHEMBL551978 YesY
Chemical data
Formula C24H31NO4 
Mol. mass 397.507 g/mol
 YesY (what is this?)  (verify)

Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, structurally related to papaverine. Drotaverine is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects.[1] Drotaverine has been shown to possess dose-dependant analgesic effects in animal models.[2] Drotaverine is sold under brand name No-Spa (Chinoin Pharmaceutical and Chemical Works, Hungary, a member of the Sanofi-Aventis)[1] and under many other names in the states of former Soviet Union (such as Kazakhstan), e.g. Но-шпа (No-shpa).